Seeking Love, Lust and Trust

Summertime

I started dating a girl over a year ago who was nice at first, but I was losing interest. She was getting fat and starting to be a pain in the ass. I decided to let her go and find a good dating site. I joined one and set up my profile with pictures and waited. My headline read, "Seeking Love, Lust and Trust". I began getting a few messages from some of the woman but none I was interested in.

Out of the blue, a hot guy messaged me, saying I was very attractive. I forgot guys could message you on this site, and I didn't know if I should respond. He did have a nice profile picture and his name was Dereck; I was tempted to but hesitated. I blew it off for a few days, then my curiosity really got to me, and I decided to respond to him. I'm 22 years old and had never been with a guy or even kissed one before. I was a tiny bit curious just to see what it would be like to kiss a guy and maybe play around with a bigger cock than mine.

Dereck was really nice to chat with at first and didn't mention sex at all. He looked like the rugged type on his profile, but his messages were very sweet. I eventually explained to him that I had never been with a guy but thought he was special. He said we should take it slow and see what happens. He seemed like the perfect guy to try a gay relationship with, and I grew fond of the idea.

After chatting for a few weeks, he asked to meet for lunch, at a burger joint, and I did. We got along great the whole time, and he paid for everything. He was fit, handsome, funny and easy to talk to. He didn't act or talk gay at all, he seemed totally straight, and we had fun hanging out together. After lunch he walked me to my car, and we exchanged cell phone numbers. Then he gave me a nice hug, flashed me a sexy smile and left.

He called me the next day, saying how great it was meeting me, and that I was very cute in person. I said it was nice to meet him too, then he asked me if I wanted to go to the movies with him the next night. I said yes and felt suddenly nervous, and my heart raced as I realized the possibilities. We ended the conversation nicely and I went back to work. I was tense and excited, getting ready for our date the next evening. I made myself look nice and made my teeth sparkle just in case he wanted to kiss me good night.

He picked me up and drove us to the movies in his fancy car. We were friendly along the way and acted just like buddies, at first. When we got in, he insisted on paying for everything and was a total gentleman. He put his arm around me briefly a few times and felt the side of my ass scooting across the aisle as we were sitting down.

During the show we just sat there and watched the movie, he didn't make any advances on me in public. I was excited and nervous for what was to come after the movie. I thought it would be nice to kiss him for being so generous. I appreciated his kindness and was willing to show that.

"What do you feel like doing now? It's not that late." He asked as we were walking out.

"I don't know." I responded cutely.

"Wanna come over my place, have a beer and listen to some music or something?" He suggested.

"Uh, OK." I said a little excited.

"Ok, let's go." He said with enthusiasm.

When we got to his car, he opened the door for me and treated me very nice. As we drove, he put his hand on mine, and I accepted his advances completely. Then I rubbed his hand a little, as we made our way to his place. When we arrived, he escorted me into his building and up to his place and showed me around. It was a nice high rise classy apartment overlooking the city.

He had a beautiful living room with plants and huge TV. He put on some soft music and grabbed us some beers. We stood out on his balcony sipping our beers and looking at the view of the city for a while, it was exhilarating. He kept his distance and played it cool with me, but I was eager to kiss him and reward him.

After we finished our beers, we sat down on his sofa and relaxed for a minute. I was starting to feel nervous and then he scooted over right next to me, which made it worse. Dereck was much bigger, and stronger than me, especially up close. I was feeling a little intimidated when he put his arm around me.

"Chrissy honey, do you like me?" He asked seriously.

"Yes." I replied innocently.

"Can I kiss you?"

"Oh, yes, please." Was all I could say.

He moved closer to my face and kissed me on the lips; he was sweet at first and it was nice. I responded by kissing him back softly and affectionately. Then he pulled me closer and began to kiss me with more desire. Our tongues touched for the first time, and they danced together passionately. It was very stimulating, feeling his big strong arm's squeezing me and being the object of his desires.

"Oh Chrissy, I really like kissing you!" He said as he broke our kisses.

"Me too." I said as my heart raced.

"You are so sexy and cute." He said in a deep voice,

Dereck continued to kiss me like a lover, with so much passion and desire. No girl had ever kissed me like this; he had so much lust and strength. Then he slid his hand down my back and began to feel my buns. I liked how he touched me, and it made me feel sexy and horny. Then he whispered in my ear in a deep sexy voice.

"You can touch mine if you want, you should feel how hard you make me!"

"Oh Dereck." I replied.

"Go ahead Chrissy, I think you will love it."

"Ok."

My shaky hand reached for his crotch and found his hard bulge. It felt very big, way bigger than mine ever was. I touched his long shaft through his pants for a few minutes; it was very stimulating. I didn't want to stop, but I was too scared to go all the way with him. I nervously rubbed his huge cock as he felt my ass, squeezing it hard and aggressively.

"Chrissy, you have a sexy ass, lets' go to my bedroom." He demanded.

"Uh, Ok." I managed to squeak out.

He got up and took my hand and lifted me to my feet. We went back to his room, and he began to remove my shirt. Then I helped him get my pants and underwear off, then I undressed him. Then he slowly began pulling down his sexy underwear, revealing a very large cock. Way big, I was shocked. He was like 10 inches long, with a big cock head. I never seen anything so big and beautiful in all my life. I couldn't stop starring, his penis took my breath away.

"Will you kiss it for me honey?" He asked.

"Oh, yes, Dereck." I said drooling with gay desires.

"Sit here on the edge of the bed." He commanded.

"OK." I said eagerly.

He put it up to my face, and I let him rub it on my cheek nicely. The big warm cock head felt nice sliding back and forth across my face. I trembled and finally grasped his super large cock and kissed it innocently. I licked the head and the sides at first, teasing his gorgeous dick. I was in awe of his strong, veiny, hard long dick. Then he forced his hard cock against my mouth, so I opened wide to please him.

I felt his monster cock filling the insides of my mouth, it felt bigger than it looked too. I wanted to be good at oral, so I tried my best to suck him with lust and care. His cock was warm, and his balls were huge too. Just as I was starting to enjoy his cock and bobbing with wild desires, he stopped me after a few minutes.

"That feels pretty good sweetie, but you have to stop for a minute." He said seriously.

"Ok." I said as I caught my breath and adjusted my jaw.

He got up and got something out of his nightstand.

"Honey, get up on the bed and bend over like a girl for me." He demanded.

"Uh, Ok." I uttered in disbelief.

Then he began to lube my ass and finger my hole forcefully. It felt good and I had to welcome his advances. He used two, then three fingers to get me ready for intercourse. I mentally prepared to take him and try this once. As he explored my asshole for the first time he spoke.

"You feel super tight Chrissy, does this hurt?" He asked as he breathed faster.

"No." I said bashfully.

"Good."

Then he popped on a condom and got behind me and teased my ass with his hard cock. He slid it up and down my crack, saying I had a cute little girly ass. He nudged my legs apart more and rubbed his cock up and down my ass crack more. He gripped my ass and stuck his thumb in hard.

"You like that Chrissy, you ready to be my little bitch?" He asked disrespectfully.

"Oh yes Dereck." I begged.

"Squeal like a girl for me."

"Oh, ok." I said surprised.

I knew my ass was going to be tight, but his cock was so hard enough to go in. Then he pushed his big fat cockhead in my hole a bit. It felt huge but I liked it, so far. He took his time working his cock in and out of my ass and was a very understanding and gentle. He made my cock hard, and my desires grew fast. I enjoyed the start of our sexual situation and encouraged him to keep going. Eventually he filled me to the max and I squealed like a girl. I felt so sexy and naughty, getting fucked by this hunk of a man.

"You are one tight little bitch, aren't you?" He said in a mean way.

"Oh Dereck, you are so big and strong" I panted.

He began to push in and out harder, penetrating me more and more. I bit my lip as I accepted this big man's physical desires. He held me firmly, taking me and taking me for a while. He stretched me out good and it felt amazing. Then he fucked me harder and faster, only pulling out and inch or two each thrust. My cock was hard and started squirting cum, I shook, and I felt the magic. Dereck kept jamming me with his big, long rod, it was awesome. I could feel him way deep inside me and I was beginning to love the sensations of our sexual friction.

"You tight little bitch!" He yelled again, as he started to slam me with all his might.

"Oh Dereck." I yelled like a sissy girl in heat.

He fucked me hard for ten minutes or so and then had to change the condom. Then he laid me on my back and made me hold up my balls. He got his hard cock up to my entrance and pushed in again, bringing me to more wonderful squirting orgasms. I liked being his little bitch now and he looked sexy and mad as he fucked me. Cum tricked out of my cock and Dereck laughed and began to jack me off.

He called me sissy now, as he fucked me relentlessly. I took it all and tried to be cute for him. My cock stayed hard the whole time as he jacked and fucked me. He smiled and kept calling me his sissy bitch, which I started to like. I wasn't asking for this role, but it was thrilling to be wanted like this, and I enjoyed being the object of his lust.

Then he held my legs up and pounded me good, he fucked me thoroughly and finally he began to orgasm. I made him cum with my ass, and I was proud to give another guy a great orgasm. I could feel the condom filling with seaman as he slowed down and his body trembled. My ass was sensitive and could feel his cock features perfectly. His cock head was felt and loved by me as it jammed in and out of me. When he finally slid his manly cock out completely, he looked sweaty, sexy and happy.

"You have the tightest little ass, Chrissy!" He said with a big smile.

"Oh, thank you Dereck." I said catching my breath.

"You are such a good little sissy girl now. You sound so sexy and cute getting fucked." He said with a laugh.

"Only for you my sexy man!" I said like an innocently.

After that, he was really nice and spooned me with his big strong, sweaty naked body. We cuddled and he kissed my ear tenderly. I felt tiny in his big strong arms and also completely desired by this hunk of a man. I could smell his manly scent and let him hold me all he wanted. His cock was pressing into my ass, and it wasn't even hard. I took on a big one for the first time and my ass did feel sore, but I was so happy.

"Would you mind being my sissy Chrissy, just for one night?" He asked nicely.

"Uh sure." I said casually, not knowing what he meant.

"Would you?" He said with excitement.

"Uh, if you'd like?" I said nicely.

"Would you wear panties and a bra?" He said with enthusiasm.

"I guess, if I have too." I said now concerned.

"Would you wear a wig and makeup?"

"If you really want too, I will." I said now overwhelmed.

"Heels and everything?"

"Uh, sure why not." I responded, now shocked.

"I think you could look like a really cute girl, if I helped you." He said seriously.

"Ok." I said, trying to be understanding.

"I think your face and body are perfect for a sissy transformation." He said with a warm smile.

"Really? Where would we do it?" I asked now worried.

"We could do it here."

"Ok." I said relieved.

"Cool, I'll get everything we need." He added.

"Ok." I said in agreement with his crazy idea.

He was sweet the rest of the night and took me home. He kissed me goodbye nicely and I was left sore for a few days, but I recovered. Dereck and I texted a lot the next few days and set up another date. He asked me to come over and play sissy the following evening. Dereck told me he raided his sisters and mothers' closet and bathroom and got us everything we need. I agreed and he asked me to shave my face, legs, arms, and body before I got there.

When I arrived at Dereck's, he welcomed me in and asked me if I shaved completely below for him, and I told him I did. Then he brought me into the master bathroom where the makeup was laid out and set to go. He helped me apply my makeup, eyelashes and wig; it was kinky and fun. I did look like a girl, when we finished. It was amazing how pretty and cute I looked. Now I had to dress the part.

He had me put on a padded bra and thong panties, to feel sexier, and I did. He gave me a red mini dress, and black heels to complete the outfit and left the room. Putting on my dress and heels was exhilarating; I looked in the mirror and couldn't believe my eyes. I looked really attractive and passable as a young woman. I felt a strange desire and rubbed my fake boobs and ass. I tapped on the door and bravely stepped out to show off my girly looks to Dereck. I was startled to see another man there. He was another hunk type and smiled at me. I was mad and glared at Dereck, feeling betrayed.

"Chrissy, this is Bill. He's an old friend of mine. He wanted to meet you." Dereck said casually.

"Hi Chrissy, you look ravishing tonight!" He said with enthusiasm and shook my hand softly.

"Hi Bill." I said in shock. Looking at Dereck like what the fuck?

"Isn't Chrissy cute Bill?"

"She sure is." He added and rubbed his cock.

Then they both approached me and began to feel me and kiss me tenderly. It was nice at first and I relaxed a bit.

"Is this OK Chrissy?" Dereck asked.

"Sure, I guess." I said getting past the shock of all this.

Then Bill began to grind me from behind and Dereck grinded me from the front. I have to admit, it was exciting being the desire of two hot men at once. So, I gave in and went along feeling safer. Bill scooped me up and carried me to the bedroom suddenly. They kissed me and felt my body, then the men began to undress me. They left me in my panties and bra and stripped off their clothes.

I was told to get on all fours and Dereck told me to suck Bill's nice cock. Dereck put a condom on and got behind me. It wasn't till then that Bill realized I really was a guy, when Dereck pulled off my thong. Bill gasped, when he saw my little dick.

"You really are a boy." Bills said in disbelief.

"This is my first time doing this." I said like insecurely.

"Isn't he cute Bill?" Dereck insisted.

"Very cute!" Bill said, now forcing me to bob on his cock, with his hand on my head.

Then Bill and Dereck started calling me Chrissy, and Sissy bitch a lot. These two men ravaged for hours me that night, taking turns, fucking me over and over, making me suck them both at once, and licking their balls. These men, treated like a sissy bitch all night. They burned through a box of condoms fucking me, and I did my best to please them with my sissy looks and noises. It was a blissful erotic evening with cum shooting off frequently. By the end we were all completely spent.

When I looked in the mirror, later that night, my makeup was smeared, and I looked like a cheap whore. These guys obviously had done a tag team before; they were just too good at it. I had fun but I didn't like being tricked like this, it was embarrassing to meet Bill like that for the first time. I removed the makeup and changed back into my clothes slept on the sofa. I tried to avoid them the rest of the night. They slept together in Dereck's bed and invited me, but I refused. It sounded like Dereck started fucking Bill, but I covered my ears went to sleep.

The next morning, I put all the girl clothes, shoes, wigs and make up in a huge garbage bag and left quietly without saying goodbye. I took the stuff as payback, and I wasn't happy with Dereck deceiving me like that. I decided to end our relationship after that night and go back to being normal.

Being a sissy was fun, and I looked really cute as a girl, but I decided to stop. A few days later, I started craving cock severely and dressed up like a girl again. I started taking lot's pics of myself with different wigs on and outfits. I used the ten second timer on my camera to take good pictures, it took all afternoon, but it was worth it. I was strangely sexy and exciting becoming Chrissy again. Wearing bras, panties and thongs was way too much fun to quit. My ass looked hot in panties or thongs, it was arousing to see myself like this.

I bought more panty hose, lingerie and other womans things online for the first time and got more familiar with my femineity. I learned to do my makeup better in just a few days and made those cat eyes like girls do, to look sexier. I really looked hotter than most girls, I was amazed at the outcome. I couldn't give this up; it was too unbelievable. My thong and panty pics looked really sexy, I was very pleased and turned on by my own photos. It took some time and effort, but becoming a woman was very stimulating.

I got bold and decided to join a gay male dating site. My profile was totally different now, with my new sissy pics and crossdresser outline. I claimed to be a sissy crossdresser eager to please, it didn't take long to get a swarm of messages. The guys came flocking and I picked the hottest ones to date. I'd meet a guy for lunch and If I liked him, I'd invite him over for some sissy fun that night.

The guys were blown away and couldn't believe I was the same person when they arrived. I was getting fucked as much as I wanted, by the hottest guys. I had repeat sex with a few guys over the next few weeks, I was becoming a slutty girl, and I loved it. I had two guys come over one night and took charge of them. Teasing them and making them both fuck me good. Then I made them suck each other, till they orgasmed. Men offered me money, trips and a place to live, because I looked so sexy and knew how to fuck a man good now. I couldn't believe the power I had over men dressed as Chrissy the sissy.

After a few sexual erotic months, I met Daniel, he really fell for me hard. He liked to kiss me in public a lot, and it was very exciting for me. I became more comfortable being a woman in public, because I was so convincing. We started dating more exclusively and it was fun being his girl. Daniel, was a gentleman and had always loved crossdressers and trans. He was thin, handsome and well hung. Rubbing cocks and doing sixty-nine sex was always a major turn on for us. It was great at the beginning.

He liked me to sound like a cute girl when he fucked, just like Dereck did. I loved how I sounded getting fucked, I could make myself sound just like a little sissy girl. After a while, Daniel was hard to please; he wanted to fuck more than I could handle, and he started to act disrespectful. My ass couldn't take his eight inches five times a day, it was too much cock for me. I tried my best and finally gave up, when he became too possessive.

Then I met a new guy online, who was very persistent, I finally gave in now that I was single again. Brad was the biggest and strongest man so far and was very handsome. After our first date we went to my place, and he ended up staying over. I had enough experience now, to please a man completely and he did as I asked.

Brad loved to be in me and loved me as Chrissy. We became close in a short time, screwing several times a day and night.

I let Brad take me that first night, because I was horny and I loved his big bulge. I was Brad's first gay encounter of any kind. Dressing like a girl, made it easier for him to open up. I led him along and broke him in. After a few weeks, we were in love, and I quit the dating site and broke a lot of hearts. He only wanted me, and I only wanted him.

Brad is 6'4" 200, with a 7" cut cock and not too thick, I'm only 5'5" and thin. The man can fuck like a horny boy all day but isn't too pushy. He understands, I need a break once in a while. He always calls me Chrissy and is very romantic. We spend our weekend's together in our world of bliss. I act like a girl all weekend and then back to work Monday as a guy.

Crossdressing has become a fun hobby. I particularly enjoy the feeling of wearing sexy panties and thongs. Brad is very respectable and sweet; he buys me flowers and lingerie all the time. I love teasing him and modeling outfits for him, he relishes our time together and melts in my hand. Controlling a man with sex is wonderful. I am so glad Dereck set me up and made me a sissy, but I'm not his sissy. I am Brads and Dereck is still begging for me back. I think it's Ok to date a sissy, be a sissy or do kinky stuff. I also insist on condoms and respect, it's been the best time of my life and it's only getting better. Cross dressing is something to consider, it's way hot!